I can’t find the suitable conditions when I react hydrazide with aldehydes. I tried to stir in RT and at reflux for days. Also, I used different solvents, like; abs ethanol, glacial acetic acid, dry DMF, DCM. In addition to adding 1ml of glacial acetic acid or few drops of triethylamine as a catalyst. But, there’s no reaction and the start material (hydrazide) is the same "no consumption"
The reaction between acid hydrazide and aldehydes to form acyl hydrazones depends on reactivity and solubility of both reactants. Usually the reaction will need heating can reach up to 24 h. Also polar aprotic solvents like DMF could help.
I am currently doing a reaction between hydrazide and coupling aldehydes for photoswitchable inhibitors. The reaction usually proceeds relatively fast at RT, with MeOH and 1h stirring, monitor through TLC.
Also if you are making the hydrazide bond yourself, the reaction reflux can take up to two days to fully convert your starting compound. For reflux I use EtOH (abs). There are few literature procedures after 2015 for your synthetic route.
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